Phenylacetyl chloride → 2,3-Dihydro-1'-(phenylacetyl)spiro[benzofuran-2,3'-pyrrolidine]

HRID 261503Notes

Reaction equation

HRID 261503 reaction equation
[C:1]1([CH2:7][C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:11]1[CH2:15][CH2:14][C:13]2([CH2:19][C:18]3[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=3[O:16]2)[CH2:12]1.Cl.N1CCC2(CC3C=CC=CC=3O2)C1.C(N(CC)CC)C>C(Cl)(Cl)Cl.O>[C:1]1([CH2:7][C:8]([N:11]2[CH2:15][CH2:14][C:13]3([CH2:19][C:18]4[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=4[O:16]3)[CH2:12]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 7679Phenylacetyl chlorideHCID 8471TriethylamineHCID 127332333H-Spiro[1-benzofuran-2,3'-pyrrolidine]HCID 203942743H-spiro[1-benzofuran-2,3'-pyrrolidine] hydrochloride

Product 1

HCID 203942702,3-Dihydro-1'-(phenylacetyl)spiro[benzofuran-2,3'-pyrrolidine]

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

A solution of 4.0 g of phenylacetyl chloride in 10 ml of chloroform is added dropwise to a stirred solution of 4.0 g of 2,3-dihydrospiro[benzofuran-2,3'-pyrrolidine], free base of Example 8, and 3 ml of triethylamine in 40 ml of chloroform. After total addition, the reaction mixture is stirred successively at ambient temperature for 18 hours and at reflux for 3 hours and then permitted to cool to ambient temperature before being poured into 100 ml of water. The organic layer is collected and then washed sequentially with dilute acid, dilute base, a saturated sodium chloride solution and dried. Thereafter, the solvent is evaporated off, leaving a dark oil which is chromatographed through a silica gel column with a 5% methyl alcohol in chloroform eluant, leaving a light yellow oil. This oil is triturated with boiling hexane, the triturant is decanted and allowed to cool, which causes a precipitate to appear. The precipitate is collected and recrystallized twice from hexane to give the pure product, 2,3-dihydro-1'-(phenylacetyl)spiro[benzofuran-2,3'-pyrrolidine], mp 98°-99° C.

Workup

  1. additionAfter total addition
  2. temperatureat reflux for 3 hours
  3. temperatureto cool to ambient temperature
  4. customThe organic layer is collected
  5. washwashed sequentially
  6. additionwith dilute acid
  7. additiondilute base
  8. dry with materiala saturated sodium chloride solution and dried
  9. customThereafter, the solvent is evaporated off
  10. customleaving a dark oil which
  11. customis chromatographed through a silica gel column with a 5% methyl alcohol in chloroform eluant
  12. customleaving a light yellow oil
  13. customThis oil is triturated with boiling hexane
  14. customthe triturant is decanted
  15. temperatureto cool
  16. customThe precipitate is collected
  17. customrecrystallized twice from hexane

Sources & evidence

ORD record
ord-2605105eb49e4ffd8e5c7d3143d2673f
Source dataset
uspto-grants-1979_08
Patent number
US04166119

Reaction notes

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